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An Insider’s Guide to September Events in the Hudson Valley

Boscobel View / Photo by Jamie Martorano

Hudson River tourism directors share their top picks for places to go, sights to see, and things to do throughout September.

We’ve said it before and we’ll say it again. There are a ton of things to do in the Hudson Valley each month. September is an especially exciting month in the area, as fall festivities begin in the way of apple picking, outdoor festivals, leaf peeper day trips, Halloween-themed attractions (a little early, but we’re not complaining), and so much more.

To help scout out the best events in the Valley, we reached out to local tourism directors from Albany to Westchester for their top picks for things to do. Check out their selections, then get planning!

Albany County

Capital District Scottish Games

Altamont Fairgrounds, Altamont
September 3, 8 a.m. – 10 p.m.

Kick off September with Celtic flare at this festival of the arts. Whether you come for the dog show, pipe bands, highland dancing, or athletic feats, you’ll be impressed by everything this fair has to offer. Take a look at the detailed schedule of events—with festivities scheduled from dawn to dusk—so you don’t miss your favorite act.

Albany Book Festival

The State University of New York at Albany, Albany
September 17, 10:30 a.m. – 5 p.m.

This free, public event celebrates all things literary with internationally acclaimed authors and workshops for aspiring writers. Workshop topics include “The Writer’s Law School: Protecting Your Artistic Rights,” “Point-of-View in Narrative Non-Fiction,” and more. Attendees can look forward to appearances from Garry Trudeau, creator of Doonesbury; Susan Choi, the award-winning author of such stories as A Person of Interest; and former US Poet Laureate Robert Pinsky.


North Pearl Street, Albany
September 17, 11 a.m.


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If you’re not quite the literary type, you can still spend your Saturday at a free, public festival in the Capital Region. Returning for the 13th year, PearlPalooza includes a lineup of local and big-name musical talent such as Phantogram, The Kaleidoscope Kid, and Precious Metals. Be sure to also join in YogaPalooza, a mass yoga gathering, if you need a Zen moment after all the excitement.

Columbia County

Roe Jan Ramble Bike Ride

Copake Memorial Park, Copake
September 17


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Join in on the 10th anniversary of this bike tour through Copake, Hillsdale, and Ancram. Choose between six routes—your choice of a 10-, 18-, 25-, 35-, 50-, or 62.5-mile ride—on some of the most scenic bike paths in all the Hudson Valley. Registration ends on September 16, meaning procrastinators are more than welcome. Once you have registered, you’ll gain access to a fundraising page which benefits the Harlem Valley Rail Trail—share it with friends and raise money for local infrastructure.

Dalmatian Day

FASNY Museum of Firefighting, Hudson
September 24, 10 a.m. – 3 p.m.

If you’ve only ever seen these spotted pups in 101 Dalmatians, this dog-themed day is a must. (It’s also a must if you have seen a dalmatian before.) At this free event, there will be a dalmatian meet-and-greet, games with prizes, craft projects, a juggling show, a puppet show, and more. Additionally, free admission to the Museum of Firefighting will be offered during the day, so be sure to stop in and make the most of your day in Hudson.

Food Truck & Craft Beer Festival

Copake Country Club, Craryville
September 24, 1-4 p.m.

Head to the first fairway for a full day of food and fun. There will be plenty of beer on tap, and attendees can look forward to samples galore. Tickets are $5 in advance and $10 day-of, so you’re well-advised to purchase them ahead of time. You can even opt to buy a VIP ticket, which affords you early entry, convenient parking, three beer tickets, a goodie bag, and access to the shaded tent.

Dutchess County

Antique Show and Flea Market

Stormville Airport, Stormville
September 3-4, 8 a.m. – 4 p.m.

For years, this has been one of the biggest flea markets in the Hudson Valley—so much so that it was featured on HGTV’s “Flea Market Flip.” Hundreds of vendors will be present, so you can stroll, shop, and snack the whole day long. Admission and parking to this rain-or-shine market are both free, and pets are not permitted. If you can’t make it this time around, look out for upcoming dates in October and November.

Hudson Valley Wine and Food Fest

Dutchess County Fairgrounds, Rhinebeck
September 10-11

Congregate with fellow foodies and oenophiles at this “premier showcase for New York wineries and gourmet specialty foods.” Attendees can choose between one of two tickets: the tasting ticket ($45/day, $80/weekend), which includes a tasting glass and samples, or the designated driver ticket ($15/day, $27/weekend) with free non-alcoholic beverages offered all day plus a souvenir tasting glass. Parking for this rain-or-shine event is free, and pets are not permitted.

Hudson Valley Rodeo With Brett Young

Keane Stud, Amenia
September 17, 12 p.m.

Grab tickets to this family-friendly event in the scenic northern Dutchess County. Spectators will be on the edge of their seats as they watch barrel racing, roping, bull riding, and more. The night will be made even sweeter by Brett Young’s performance after the rodeo. The multi-platinum singer wows audiences with his “West Coast-meets-Southern” style and has dropped seven consecutive No. 1 hits.

Orange County

Uncle Shoehorn’s Funky Corn Festival

Wright Family Farm, Warwick
September 3, 12-6 p.m.

Begin your September in the Hudson Valley with this quirky event on a family farm. You can look forward to a teaser of fall in the way of corn mazes, pumpkin cannons, corn treats, and a cornhole tournament. The event will take place rain or shine, and the Wright family kindly requests that patrons leave their dogs and coolers at home—though the latter shouldn’t be an issue, as local craft beer, cider, and wine will be available at the festival.

Butterfly Day

Hudson Highlands Nature Museum, Cornwall
September 10, 10 a.m. – 3 p.m.

Don’t miss out on 30 minutes inside the butterfly tent! Get up close to these beautiful creatures, as well as moths and caterpillars, at the Hudson Highlands Nature Museum’s butterfly enclosure. Attendees are encouraged to explore the museum grounds and watch the tagging and release of monarch butterflies at noon and 3 p.m. “Not-yet members”—as the museum dubs them—pay $12, whereas members pay $8. Children three and under enter free.

Pure Terror Scream Park

Museum Village, Monroe
Friday – Sunday, September 24 – October 30

Halloween has arrived early…if you can handle it. Can you brave the Hudson Valley’s most haunted pathway? Spanning for 1.2 miles of spookiness, this destination holds a Guinness World Record for the longest walk-through horror attraction. With 10 haunted houses onsite, terribly talented actors, ghoulish sets, and special effects, you’ll forget it’s all an act you paid to see. Or is it? Cue the maniacal laughter.

Putnam County

Hearts of the Hollow

Whipple Feeley Chapel, Carmel
September 9 – October 31

What do you get when you cross Washington Irving’s iconic short story, “The Legend of Sleepy Hollow,” with musical theater? You get Hearts of the Hollow, a two-act, 20-song interpretation of the story. Just like the tale by Irving—who lived in Westchester—this musical is set in the Hudson Valley, opening on a battlefield in White Plains. The songs, as performed by the Prague Philharmonic Chamber Orchestra, include “heartwarming ballads, cheerful up-tempo numbers, and…some hair-raising scores of villainy!”

Patterson Rotary Blues & Barbecue Festival

Patterson Fire Department, Patterson
September 17-18


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We’ve got two questions for you. Do you like barbecue? And do you like the blues? If you answered yes to either of those, you’ll have a ball at this Putnam County festival. Musicians like Doug Deming & the Jewel Tones, Pat O’Shea, Fade to Blues, and Night Train Express will help make this the bluesiest bash in all the Hudson Valley.

Vietnam Veterans Memorial Traveling Wall

Putnam County Veterans Memorial Park, Carmel
September 22-25

While Veterans Day isn’t until November, this traveling memorial site is a perfect way to commemorate those lost in combat. The Traveling Wall is an 80-percent scaled replica of the Vietnam Veterans Memorial in Washington D.C. Volunteers will read aloud all 58,318 names on the wall. An opening ceremony will be held on September 22 at 7 p.m., and a closing ceremony will be held on September 25 at 11 a.m. with a performance by The Hudson Valley Council Band.

Rockland County

Phoenix Festival

September 16 – October 16

In its inaugural year, this festival will celebrate theater, music, and art over the course of five weekends. It will host international talent at one of three venues—see the website for more on that—promoting the arts and Rockland County alike. Every performance will take place with “a backdrop of majestic Hudson River vistas,” making this festival as scenic as it is sensational.


The Historical Society of Rockland County, New City
September 18, 12-5 p.m.

If your idea of a good time involves a whole lot of history, then this event will be the highlight of your September in the Valley. The special feature of the day is a performance of Guns at the Gateway!—a play written and presented by Sean Grady and Gary Petagine—which will mark the 242nd anniversary of the infamous Arnold-Andre affair. Additionally, attendees can look forward to lawn games, scavenger hunts, 18th-century arts and crafts, tours of the Historic Jacob Blauvelt Farmhouse (at 1, 3, and 4 p.m.), and—perhaps most important of all—complimentary cider donuts. Admission to this rain-or-shine event is free, though you’ll have to cough up a $5 to participate in the activities.

The Flavors of Haverstraw Food Crawl

Downtown Haverstraw
September 18, 1-5 p.m.

To celebrate their diverse culinary community, Haverstraw Riverwide Arts and the Village of Haverstraw have teamed up to present this restaurant crawl to the foodies of the Hudson Valley and beyond. Beginning at the Webster Bank parking lot on New Main Street, participants can drink and dine at over 15 participating restaurants for $5-$10 per plate. Tents, tables, and chairs will be set up for foodies who prefer not to dine indoors.

Ulster County

Woodstock-New Paltz Arts & Crafts Fair

Ulster County Fairgrounds, New Paltz
September 3-4, 10 a.m. – 5:30 p.m.; September 5, 10 a.m. – 4 p.m.

DIY interior designers and craft lovers in the Hudson Valley should plan a visit to this fair over Labor Day weekend. The fair packs over 200 juried artists and craftspeople onto the Ulster County Fairgrounds to celebrate the region’s foremost craftspeople. With shopping, children’s activities, and massage therapy as only a few of the onsite attractions, this event is one for the books.

Benjamin Wigfall and Communications Village

The Dorsky, New Paltz
September 10 – December 11

Art appreciators won’t want to miss this first retrospective of Benjamin Wigfall, an abstract artist who taught at SUNY New Paltz and “intentionally established his studio in a close-knit Black neighborhood in nearby Kingston” called Communications Village. His studio became a haven for fellow Black visual artists to delve into printmaking and interact with the Kingston community at large. The work on display spans from his early career in 1950s Virginia to his work with the Village throughout the ’70s.

Apple Festival

Esopus United Methodist Church, Port Ewen
September 24, 8 a.m. – 3 p.m.

It’s September in the Hudson Valley, so it comes as no surprise that there is at least one apple-themed festival on our tourism guide. If you come early enough, you might be able to get your hands on a whole apple pie—be forewarned, they sell out fast. Additional victuals include apple pie slices served a la mode, fried dough, sausage and peppers, burgers, hot dogs, and your everyday, plain ol’ apple—fresh from the orchard, of course.

Westchester County

Afternoon Tea

Caramoor, Katonah
September 9, 16, and 23, 2 p.m.


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Care for a spot of tea? Spend an afternoon with close friends at a formal tea service in Caramoor’s ornate Rosen House Music Room. Choose from the selection of teas and nibble on bites like tea sandwiches, scones with crème fraiche and preserves, and more on vintage china. Patrons have the opportunity to tour the Rosen House, but should reserve a spot to do so in advance.

The Great Jack-o’-Lantern Blaze

Van Cortlandt Manor, Croton-on-Hudson
September 16 – November 20

Where else can you stroll through an 18th-century landscape and soak in the candlelight emanating from within 7,000 jack-o’-lanterns than Westchester’s Van Cortlandt Manor? Every single squash is designed and carved by a team of artisans. Spooky as it may be, you can’t help but appreciate the incredible artistry that goes into this Halloween event. The display is open on various nights throughout the fall, so be sure to check the schedule online before planning your trip.


Bedford Village Green, Bedford
September 24, 6:30-9:30 p.m.

Get your palates ready for the seventh annual Hoppfest, which promises to be better and “beerier” than ever before. Attendees are well advised to “wear their dancing shoes,” as there will be live music all evening long as well as wine, beer, and bourbon tastings; pub games; fire pits; and more. If you need a little grub between beers, the food trucks will come in clutch. Purchase your ticket—which covers everything except the food trucks—online.

Related: Your Official Hudson Valley Apple Picking Farm Guide

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